From Online to In-Person: Navigating the First Date

How to take the conversation from the web to face-to-face.

All right, so now you’re all set with a shiny dating profile that’s garnered lots of hits from potential hotties. You’ve winnowed through the pool and chosen your potential catch. Now, it’s time to actually link up with “the one”—or one of the ones—beyond the digital realm and in reality.

It's always your best bet to take your Internet conversation into the real world as soon as possible before you establish a virtual rapport that can become awkward and stilted when it has to translate into face-to-face. So, if you've exchanged a couple flirtatious messages with a potential mate, established a basic foundation of things you have in common and are somewhat assured that it's worth testing the waters with a meet-up, take the plunge and ask her to hang out.

First meetings, especially those catalyzed on the Internet don’t have to be complicated, but there are a few caveats to heed prior to jumping in. To have the best possible time, while preserving your physical and mental wellbeing, read on.

Think About it From Her Point of View

Your first meeting is about you, certainly, but says psychologist, sex therapist, advice columnist, speaker and author, Dr. Joy Davidson, the stakes are generally higher for her. “Remember that getting ready for a first ‘meet-up’ takes as much time and effort for a woman as a real first date,” Davidson explains. “She’ll spend time doing her hair, applying her makeup oh-so-perfectly, choosing the right outfit—all of which is easily an hour or more out of her day. You won’t be spending the same amount of prep time, so consider that her investment has already trumped yours, and make it worth her while.”

Davidson suggests that you meet somewhere that you’d take a “real” first date, not just a “check-her-out” prospect. “You needn’t go so far as to spring for dinner, but a drink in a nice environment, or even lunch, will make a far better impression than coffee at the local Starbucks,” she says. “By treating her with respect, picking up the check, and in general being cool, you’ll win points. Granted, if you two don’t click, they might just be karma points, but if there’s chemistry, you’ll have avoided turning her off by lacking finesse.”

Note Your Nearest Emergency Exit

Most online dating advice regarding safety is geared toward women, and not without good reason. Sexual predators constantly troll the Internet looking for prey, and ladies who trust too easily can, and do, wind up in compromising or even dangerous situations.

Women are told to A) Meet their date in a public, B) Let someone know where they'll be and with whom, C) Bring a cell phone, and D) Have an exit strategy. Think about that for a minute. No matter how hot you are for her, or how hot she seems to be for you online, in person, the first thing she’s going to try to suss out is whether or not you’re to be trusted. It’s no reflection on you, and it doesn't matter if you spend your Sundays helping out at the local orphanage or old folks home. So if she's being a little less forthcoming with personal information or unwilling to go somewhere more private, she’s exercising common sense. Let her, and also bear in mind that common sense works both ways—the aforementioned cautions all hold merit, for her as well as for you.

Red Flags

One of the biggest mistakes of online communication is thinking a relationship forged from over-sharing is the real deal. There’s always the chance that the person you got to know online isn’t what she seems. Men aren’t the only predators hunting for their next mark or broken toys searching for someone who can “fix them.” If your date is too eager too soon, or seems a little too interested in your personal finances, or for some reason just makes the hair on your arms stand up—and not in a good way—it’s best to proceed with caution, if at all.

“If someone starts talking about the future at the first meeting, or even if she jumps into bed with [you] the same night (unless it was a sex match-up site), be on the lookout for a clingy, dependent type,” Davidson warns. “Also watch the type of questions she asks. Some information will be designed to ensure her own safety; other information is just inappropriate—like discussing or asking about intimate details of past relationships early on. Usually, if something feels ‘weird’ or ‘off,’ it probably is, so trust your instincts.”

Finally, Davidson notes, guys should avoid getting so wrapped up in their own fantasies about someone that they miss the cues that would otherwise tell them she’s not right for them. “Sometimes we are our own worst enemies in that when our hopes and fantasies clash with reality, we tend to over-focus on the fantasy and make excuses for or rationalize the reality,” she explains. “Men are just as prone to this as women. I’d advise the same degree of self-awareness that I’d suggest to women in order to avoid the mess that can ensue as a result.”

If your Spidey Sense tells you something’s amiss—say she’s 10 years older than she led you to believe, swapped out her pic for someone else’s on her profile, or invites you to her sister’s wedding for your next date—there’s nothing wrong with cutting your losses, as long as you do it tactfully. (No matter how bad/scary the date may be, flirting with the waitress—or any woman who isn’t your date, or worse, excusing yourself to the men’s room and leaving her with the bill is not acceptable behavior.)

All’s Well That Ends Well

According to Davidson, the end of a meet-up date can be awkward, especially if you aren’t sure if you want to see her again. “One way to handle it is to say something like, ‘I’ve really enjoyed spending time with you. Why don’t we both think about how we feel about another date. I’ll email (or text, or IM) you later.’ Then be sure you do it,” she says. “On the other hand, if you’re certain you want to see her again, before you part, suggest getting together over the weekend. Then follow up in less than a day with suggestions for your next date. Meaning what you say and doing what you promise will show that you are a quality guy. Playing it ‘cool’ by being unavailable, or simply lacking follow-through, will make any smart woman think twice about trusting you with her time, let alone her heart.”

And if it turns out it’s just a case of you’re just not that into her? Man up. If you’re out for a meal or drinks, pick up the tab, but do not tell her you’ll be calling if you won’t. Find a way to explain, as nicely as you can, that you’re not feeling the need to go forward, then say goodbye. “Just say that as much as you enjoyed getting to know her, you realized you two weren’t quite the match you’d hoped,” Davidson advises. “Thank her for the date, and wish her well in her search for Mr. Right.”

Will you feel like you’re shooting a puppy? Perhaps, but it’s a lot less cruel in the long run than leading her on. Will she analyze it to death, beat herself up, and second-guess every word that came out of her mouth? More than likely, but your karma will be clean, and you can move on to the next Miss Right with a clear conscience.